Molecular Network-Guided Alkaloid Profiling of Aerial Parts of Papaver nudicaule L. Using LC-HRMS

Abstract

Papaver nudicaule L. (Iceland poppy) is widely used for ornamental purposes. A previous study demonstrated the alleviation of lipopolysaccharide-induced inflammation mediated by P. nudicaule extract through nuclear factor-kappa B and signal transducer and activator of transcription 3 inactivation. As isoquinoline alkaloids are chemical markers and bioactive constituents of Papaver species, the present study investigated the alkaloid profile of aerial parts of five P. nudicaule cultivars with different flower colors and a P. rhoeas cropped for two years. A combination of liquid chromatography high-resolution mass spectrometry and molecular networking was used to cluster isoquinoline alkaloids in the species and highlight the possible metabolites. Aside from the 12 compounds, including rotundine, muramine, and allocryptopine, identified from Global Natural Products Social library and reported information, 46 structurally related metabolites were quantitatively investigated. Forty-two and 16 compounds were proposed for chemical profiles of P. nudicaule and P. rhoeas, respectively. Some species-specific metabolites showed similar fragmentation patterns. The alkaloid abundance of P. nudicaule differed depending on the flower color, and the possible chemical markers were proposed. These results show that molecular networking-guided dereplication allows investigation of unidentified metabolites. The derived chemical profile may facilitate evaluation of P. nudicaule quality for pharmacological applications.

Ethyl Acetate Fractions of Papaver rhoeas L. and Papaver nudicaule L. Exert Antioxidant and Anti-Inflammatory Activities

“…Among them, 493 metabolites showed a strong negative correlation between the EtOAc group and inhibitory effects on LPS-induced NO production. Identifying relevant active molecules from complex mixtures represents a major challenge in natural product drug discovery [ 22 , 37 , 38 ], and identified metabolites ( Table S1 ) were labeled on the integrated correlation to obtain potent bioactive compound information and dereplicate effectively ( Figure 7 a). To investigate potentially bioactive metabolites in compound mixtures from EtOAc fractions and EtOH extracts, significant metabolites represent potent metabolites with a statistically significantly strong biochemometric value (strong Pearson correlation value (r < −0.7) and significance (FDR-corrected, p value < 0.05)) and a higher average of peak area.…”

“…To investigate the anti-inflammatory and antioxidant properties of phytochemicals, liquid chromatography coupled with quadrupole time-of-flight mass spectrometry-based alkaloid profiling of EtOH extracts and EtOAc fractions was performed using chromatographic analysis, as previously reported [ 22 ]. Profiling data acquired from 12 samples, including EtOH extracts and EtOAc fractions of P. nudicaule and P. rhoeas in the untargeted scan were processed using MarkerView 1.3.1 (SCIEX, Foster City, CA, USA).…”

“…P. nudicaule has been used as a mild diaphoretic and a source of vitamin C [ 17 , 18 ]. Papaver species produce various alkaloids, particularly isoquinoline alkaloids, which have potent pharmacological activities such as narcotic analgesic, antimicrobial, cough suppressant, and anticancer effects [ 15 , 19 , 20 , 21 , 22 ]. Recent studies have also confirmed various pharmacological effects of P. rhoeas extracts, including antioxidant, cytoprotective, antimicrobial, antimutagenic, anti-analgesic, and antiulcerogenic activities [ 15 , 19 , 23 , 24 , 25 , 26 , 27 ].…”

Hetiamacin E and F, New Amicoumacin Antibiotics from Bacillus subtilis PJS Using MS/MS-Based Molecular Networking

“…The aim of this research was to deeply investigate the novel metabolites in fermentation extracts of B. subtilis PJS by using a recently developed cheminformatic approach, molecular networking [ 4 ]. As a visualization tool designed to address structural elucidation of different compounds, molecular networking is compatible with early identification of new molecules that are related to known substances and provides opportunities to identify new molecular families from complex mixtures [ 34 , 35 , 36 ]. The application of molecular networking in our latest studies have successfully contributed to the discovery of some new chemical entities, such as the discovery of new streptogramin-type antibiotics, acetyl-griseoviridin, and desulphurizing griseoviridin in the fermentation broth of Streptomyces sp.…”

Erratum: Song, K.; et al. Molecular Network-Guided Alkaloid Profiling of Aerial Parts of Papaver nudicaule L. Using LC-HRMS. Molecules 2020, 25, 2636

“…The authors wish to make the following change to their paper [ 1 ]. The Funding section is incorrect in the published paper.…”